That's the compulsive Mackler himself dressed in full Jewface for a surprise show in Seattle this year. How do you go from rapping against hurtful stereotypes to actually embodying one? Well, if you believe Macklemore's version, it all happened due to a series of unhappy coincidences, which if true would be enough to convince anyone that Yahweh is real (and hates rap music).
Macklemore says that, since it was a secret concert and all, he had the idea to surprise the audience by showing up in a disguise. Without any specific look in mind, he went to a local costume store and bought some fake beards, mustaches, and "a big witch nose," which he combined with a wig he had from a previous tour (presumably from his time in a Beatles cover band). Coincidence #1 would be the fact that these random items just happened to form an image straight out of the imagination of a Stormfront forumgoer; #2 is that in all of Macklemore's entourage, there wasn't a single sane human being to tell him what he looked like.
Suzi Pratt/FilmMagic/Getty Images, Henry Mayo Bateman
They did talk him out of wearing that "extremely small beanie" he found in a synagogue.
Mackleberg then revealed himself to the audience and played a few songs, including his hit "Thrift Shop" -- you know, that catchy tune about how buying stuff for cheap is "fucking awesome." Apparently, the rapper didn't even suspect that this might have been a poor choice (or several) until he found out he'd pissed off at least one influential Jewish leader: